US9121041B2 - Method for the preparation of diols - Google Patents

Method for the preparation of diols Download PDF

Info

Publication number
US9121041B2
US9121041B2 US13/169,703 US201113169703A US9121041B2 US 9121041 B2 US9121041 B2 US 9121041B2 US 201113169703 A US201113169703 A US 201113169703A US 9121041 B2 US9121041 B2 US 9121041B2
Authority
US
United States
Prior art keywords
gene
region
microorganism
sequence
strain
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US13/169,703
Other languages
English (en)
Other versions
US20110294178A1 (en
Inventor
Philippe Soucaille
Cédric Boisart
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Metabolic Explorer SA
Original Assignee
Metabolic Explorer SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Metabolic Explorer SA filed Critical Metabolic Explorer SA
Priority to US13/169,703 priority Critical patent/US9121041B2/en
Assigned to METABOLIC EXPLORER reassignment METABOLIC EXPLORER ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SOUCAILLE, PHILIPPE
Publication of US20110294178A1 publication Critical patent/US20110294178A1/en
Application granted granted Critical
Publication of US9121041B2 publication Critical patent/US9121041B2/en
Expired - Fee Related legal-status Critical Current
Adjusted expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20—Bacteria; Culture media therefor
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/005—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor after treatment of microbial biomass not covered by C12N1/02 - C12N1/08
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/70—Vectors or expression systems specially adapted for E. coli
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic

Definitions

  • the present invention concerns a microorganism genetically modified for the bioproduction of an aliphatic diol, wherein the microorganism comprises a metabolic pathway for the decarboxylation of a hydroxy-2-keto-aliphatic acid metabolite with an enzyme having a 2-keto acid decarboxylase activity, the product obtained from said decarboxylation step being further reduced into the corresponding aliphatic diol with an enzyme having a hydroxy aldehyde reductase activity, and wherein the microorganism is genetically modified for the improved production of said hydroxy-2-keto-aliphatic acid metabolite.
  • the term “microorganism” designates a bacterium, yeast or a fungus.
  • the microorganism is selected among Enterobacteriaceae, Clostridiaceae, Bacillaceae, Streptomycetaceae and Corynebacteriaceae.
  • the microorganism is a species of Escherichia, Clostridium, Bacillus, Klebsiella, Pantoea, Salmonella or Corynebacterium .
  • the microorganism is either the species Escherichia coli or Corynebacterium glutamicum or Clostridium acetobutylicum or Bacillus subtilis.
  • genes and proteins are generally identified using the denominations of genes from Escherichia coli . However, use of these denominations has a more general meaning according to the invention and covers all the corresponding genes and proteins in other organisms, more particularly microorganisms, functional homologues, functional variants and functional fragments of said genes and proteins.
  • the microorganism is modified to present an attenuated level of homoserine conversion to other compounds than 1,3-propanediol.
  • This result may be achieved by attenuating the level of homoserine consuming enzymes like homoserine kinase and threonine synthase (encoded by thrB and thrC), homoserine O-transsuccinylase (encoded by metA) or dihydrodipicolinate synthase (encoded by dapA).
  • homoserine kinase and threonine synthase encoded by thrB and thrC
  • homoserine O-transsuccinylase encoded by metA
  • dihydrodipicolinate synthase encoded by dapA.
  • These genes can be attenuated by replacing the natural promoter by a weaker promoter or by elements destabilizing the corresponding messenger RNA or protein. If needed, complete attenuation of
  • the PCR amplified fragment was cut with the restriction enzymes SnaBI and BglII and cloned into the SnaBI-BglII sites of the vector pME101-kivDll-TT07 resulting in the vector pME101-kivDll-yqhD-TT07.
  • the kanamycin resistant transformants were then selected and the ⁇ pykF::Km was verified by a PCR analysis with the previously defined oligonucleotides pykFF and pykFR.
  • the strain retained was designated MG1655 ⁇ sdaA ⁇ sdaB ⁇ pykF::Km.
  • phage P1 transduction was used.
  • the preparation of the phage lysate of the strain MG1655 ⁇ pykF::Km (described above) was used for the transduction into the strain MG1655 ⁇ metA.
  • the protein was purified from crude cell-extract by affinity on a Profinity column (BIORAD, Bio-Scale Mini Profinity exact cartridge 5 ml) according to the protocol recommended by the manufacturer. Crude extract was loaded on a 5 ml Profinity exact cartridge equilibrated with 100 mM potassium phosphate pH 7.6. The column was washed with 10 column volumes of the same buffer and incubated overnight with 100 mM potassium phosphate pH 7.6, 100 mM fluoride at 4° C. The protein was eluted from the column with 2 column volumes of 100 mM potassium phosphate pH 7.6. The tag remained tightly bound to the resin and the purified protein was released. The fractions containing the protein were pooled and dialyzed against 100 mM potassium phosphate, 150 mM NaCl and 10% glycerol pH 8.
  • yqhDF (SEQ ID NO 80): ggcgtctcgccatacaacaacgcacatcgggc (homologous to the sequence from 3153068 to 3153100).
  • yqhDR (SEQ ID NO 81): gggctttgccgacaccttcttcgttcttg (homologous to the sequence from 3154825 to 3154797).
  • the pTRC99A-yqhD plasmid was then introduced into the strain MG1655 ⁇ yqhD::Km.
  • the pPAL7-serC plasmid was then introduced into competent BL21 (DE3) cells (Invitrogen).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Sustainable Development (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
US13/169,703 2008-12-31 2011-06-27 Method for the preparation of diols Expired - Fee Related US9121041B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/169,703 US9121041B2 (en) 2008-12-31 2011-06-27 Method for the preparation of diols

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US14169908P 2008-12-31 2008-12-31
EP08173129.1 2008-12-31
EP08173129 2008-12-31
EP08173129 2008-12-31
US36145909P 2009-07-05 2009-07-05
PCT/EP2009/067994 WO2010076324A1 (en) 2008-12-31 2009-12-29 Method for the preparation of diols
US13/169,703 US9121041B2 (en) 2008-12-31 2011-06-27 Method for the preparation of diols

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/067994 Continuation-In-Part WO2010076324A1 (en) 2008-12-31 2009-12-29 Method for the preparation of diols

Publications (2)

Publication Number Publication Date
US20110294178A1 US20110294178A1 (en) 2011-12-01
US9121041B2 true US9121041B2 (en) 2015-09-01

Family

ID=40637987

Family Applications (1)

Application Number Title Priority Date Filing Date
US13/169,703 Expired - Fee Related US9121041B2 (en) 2008-12-31 2011-06-27 Method for the preparation of diols

Country Status (10)

Country Link
US (1) US9121041B2 (de)
EP (1) EP2379730B1 (de)
JP (1) JP5774493B2 (de)
KR (2) KR20110117131A (de)
CN (1) CN102341502B (de)
BR (1) BRPI0923748B1 (de)
ES (1) ES2549003T3 (de)
MX (1) MX2011007039A (de)
PT (1) PT2379730E (de)
WO (1) WO2010076324A1 (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2396907T3 (es) 2006-06-02 2013-03-01 Fresenius Medical Care Deutschland Gmbh Recipiente lleno de un concentrado líquido para preparar un líquido de diálisis
SG176656A1 (en) 2009-06-04 2012-01-30 Genomatica Inc Microorganisms for the production of 1,4-butanediol and related methods
US20110312049A1 (en) * 2010-04-13 2011-12-22 Osterhout Robin E Microorganisms and methods for the production of ethylene glycol
TWI500768B (zh) * 2010-07-05 2015-09-21 Metabolic Explorer Sa 由蔗糖製備１，３－丙二醇之方法
EP2635673B1 (de) * 2010-11-03 2020-05-20 The Regents of The University of California Biokraftstoff- und chemikalienproduktion mithilfe rekombinanter mikroorganismen durch fermentation einer proteinhaltigen biomasse
EP2503003A1 (de) * 2011-03-24 2012-09-26 Volker Sieber Syntheseweg zur Herstellung von Alkoholen und Aminen
WO2012177983A2 (en) * 2011-06-22 2012-12-27 Genomatica, Inc. Microorganisms for producing ethylene glycol and methods related thereto
EP2540834A1 (de) 2011-06-29 2013-01-02 Metabolic Explorer Verfahren zur Herstellung von 1,3-Propandiol
US9914947B2 (en) * 2011-07-27 2018-03-13 Alliance For Sustainable Energy, Llc Biological production of organic compounds
AU2012318597A1 (en) * 2011-10-05 2014-04-24 The Procter & Gamble Company Microorganisms and methods for producing acrylate and other products from homoserine
EP2783007B9 (de) 2011-11-21 2018-03-28 Metabolic Explorer Mikroorganismusstämme zur herstellung von 2,3-butandiol
WO2013126721A1 (en) * 2012-02-23 2013-08-29 Massachusetts Institute Of Technology Engineering microbes and metabolic pathways for the production of ethylene glycol
SI2855687T1 (sl) 2012-06-04 2020-09-30 Genomatica, Inc. Mikroorganizmi in metode za proizvodnjo 4-hidroksibutirat, 1,4-butandiola in sorodne spojine
WO2014004625A1 (en) * 2012-06-26 2014-01-03 Genomatica, Inc. Microorganisms for producing ethylene glycol using synthesis gas
KR102093172B1 (ko) * 2012-07-11 2020-03-25 아디쎄오 프랑스 에스에이에스 2,4-다이하이드록시부티레이트의 제조 방법
WO2014037912A2 (en) * 2012-09-07 2014-03-13 Cellworks Research India Pvt. Ltd Methods for production of isobutanol through nutrient stress and genetically modified microorganisms thereof
WO2014049382A2 (en) 2012-09-26 2014-04-03 Metabolic Explorer Ethylenediamine fermentative production by a recombinant microorganism
KR102113254B1 (ko) 2013-08-23 2020-05-21 삼성전자주식회사 1,4―ｂｄｏ 생산을 위한 유전자 스크리닝 방법
EP2930244A1 (de) * 2014-04-07 2015-10-14 The Procter and Gamble Company Mikroorganismen und Verfahren zur Herstellung von Acrylat- und anderen Produkten aus Homoserin
WO2015167043A1 (ko) * 2014-04-30 2015-11-05 삼성전자 주식회사 증가된 알파-케토글루타레이트 데카르복실라제 활성을 갖는 미생물 및 이를 이용한 1,4-부탄디올 생산방법
US10385322B2 (en) 2014-10-03 2019-08-20 Metabolic Explorer Mutant glutamate dehydrogenase for the conversion of homoserine into 4-hydroxy-2-ketobutyrate
WO2016094526A1 (en) * 2014-12-11 2016-06-16 Ciris Energy Inc. Genetically modified microbes for the biological conversion of carbonaceous materials to diols
SG11201705988UA (en) 2015-02-24 2017-08-30 Bioatla Llc Conditionally active biological proteins
US20180179499A1 (en) 2015-06-04 2018-06-28 Bioamber Inc. Biobased production of functionalized alpha-substituted acrylates and c4-dicarboxylates
DK3365427T3 (da) 2015-10-23 2020-10-26 Metabolic Explorer Sa Mikroorganisme, der er modificeret til assimilation af levulinsyre
CN105441372A (zh) * 2015-10-30 2016-03-30 清华大学 一种重组谷氨酸棒杆菌与应用
AU2017291975B2 (en) 2016-07-08 2021-06-03 Metabolic Explorer Method for the fermentative production of molecules of interest by microorganisms comprising genes coding sugar phosphotransferase system (PPS)
CN106957878B (zh) * 2017-04-19 2020-10-30 波顿（上海）生物技术有限公司 一种生物催化生产2-苯乙醇的方法
EP3470512A1 (de) 2017-10-10 2019-04-17 Metabolic Explorer Mutierte phosphoserin-aminotransferase für die konversion von homoserin zu 4-hydroxy-2-ketobutyrat
JP2022520814A (ja) 2019-02-15 2022-04-01 ブラスケム エス．エー． 逆グリオキシル酸短絡を通じたグリコール酸およびグリシンの生成のための微生物および方法
CN113710798A (zh) 2019-02-20 2021-11-26 布拉斯科公司 戊糖和己糖的降解途径
CN113710807A (zh) 2019-02-20 2021-11-26 布拉斯科公司 用于由己糖生产含氧化合物的微生物和方法
WO2021004614A1 (en) * 2019-07-08 2021-01-14 Symrise Ag Biotechnological production of diols
CN111349643B (zh) * 2020-03-17 2022-06-24 花安堂生物科技集团有限公司 生物合成异戊二醇的菌株及方法
WO2023069957A1 (en) * 2021-10-20 2023-04-27 Genomatica, Inc. Aldehyde dehydrogenase variants and methods of use
CN116355821B (zh) * 2023-03-10 2023-09-29 湖北大学 一种生产乙二醇的运动发酵单胞菌重组菌株、构建方法及其应用

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0620853A1 (de) 1991-12-12 1994-10-26 Wacker Chemie Gmbh Materialien und verfahren zur biosynthese von serinen und serinverwandten produkten.
WO1996035796A1 (en) 1995-05-12 1996-11-14 E.I. Du Pont De Nemours And Company Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism
EP0931833A2 (de) 1998-01-12 1999-07-28 Ajinomoto Co., Inc. Methode zur Herstellung von L-Serin mittels Fermentation
WO2001012833A2 (en) 1999-08-18 2001-02-22 E.I. Du Pont De Nemours And Company Process for the biological production of 1,3-propanediol
WO2004033646A2 (en) 2002-10-04 2004-04-22 E.I. Du Pont De Nemours And Company Process for the biological production of 1,3-propanediol with high yield
WO2004076659A2 (fr) 2003-02-18 2004-09-10 Metabolic Explorer Procede de preparation de microorganismes evolues permettant la creation ou la modification de voies metaboliques
EP1496111A2 (de) 2003-07-10 2005-01-12 Consortium für elektrochemische Industrie GmbH Varianten der 3-Phosphoglyceratdehydrogenase mit reduzierter Hemmung durch L-Serin und dafür codierende Gene
WO2005047498A1 (fr) 2003-11-06 2005-05-26 Metabolic Explorer Souches de microorganismes optimisees pour des voies de biosynthese consommatrices de nadph
WO2005073364A2 (fr) 2004-01-12 2005-08-11 Metabolic Explorer Microorganisme evolue pour la production de 1,2-propanediol
WO2005111202A1 (en) 2004-05-12 2005-11-24 Metabolic Explorer Recombinant enzyme with altered feedback sensitivity
WO2006082254A2 (en) 2005-02-07 2006-08-10 Metabolic Explorer Microorganisms comprising enzymes expressed with low gamma-elimination activity
WO2006082252A2 (en) 2005-02-07 2006-08-10 Metabolic Explorer Method for the enzymatic production of alpha-ketobutyrate
WO2007017710A1 (en) 2005-08-11 2007-02-15 Metabolic Explorer Process for the preparation of aspartate and derived amino acids like lysine, threonine, isoleucine, methionine, homoserine, or valine employing a microorganism with enhanced isocitrate lyase and/or malate synthase expression
WO2007077041A1 (en) 2006-01-04 2007-07-12 Metabolic Explorer Process for the preparation of methionine and its precursors homoserine or succinylhomoserine employing a microorganism with enhanced sulfate permease expression
US7267972B2 (en) 1999-07-09 2007-09-11 Institut National De La Recherche Method for preparing 1,3-propanediol by a recombinant micro-organism in the absence of coenzyme b12 or one of its precursors
US20070259411A1 (en) * 2006-05-05 2007-11-08 Bramucci Michael G Solvent tolerant microorganisms and methods of isolation
WO2007141316A2 (en) 2006-06-09 2007-12-13 Metabolic Explorer Glycolic acid production by fermentation from renewable resources
WO2007144346A1 (en) 2006-06-12 2007-12-21 Metabolic Explorer Ethanolamine production by fermentation
WO2008040387A1 (en) 2006-10-03 2008-04-10 Metabolic Explorer Process for chromosomal integration and dna sequence replacement in clostridia
WO2008052595A1 (en) 2006-10-31 2008-05-08 Metabolic Explorer Process for the biological production of 1,3-propanediol from glycerol with high yield
WO2008052973A2 (en) 2006-10-31 2008-05-08 Metabolic Explorer Process for the biological production of n-butanol with high yield
WO2008115840A2 (en) 2007-03-16 2008-09-25 Genomatica, Inc. Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0807235A2 (pt) 2007-02-09 2015-05-26 Univ California Microorganismo recombinante, e, métodos para produzir um microorganismo recombinante, e para produzir um álcool

Patent Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0620853A1 (de) 1991-12-12 1994-10-26 Wacker Chemie Gmbh Materialien und verfahren zur biosynthese von serinen und serinverwandten produkten.
WO1996035796A1 (en) 1995-05-12 1996-11-14 E.I. Du Pont De Nemours And Company Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism
EP0931833A2 (de) 1998-01-12 1999-07-28 Ajinomoto Co., Inc. Methode zur Herstellung von L-Serin mittels Fermentation
US7267972B2 (en) 1999-07-09 2007-09-11 Institut National De La Recherche Method for preparing 1,3-propanediol by a recombinant micro-organism in the absence of coenzyme b12 or one of its precursors
WO2001012833A2 (en) 1999-08-18 2001-02-22 E.I. Du Pont De Nemours And Company Process for the biological production of 1,3-propanediol
WO2004033646A2 (en) 2002-10-04 2004-04-22 E.I. Du Pont De Nemours And Company Process for the biological production of 1,3-propanediol with high yield
WO2004076659A2 (fr) 2003-02-18 2004-09-10 Metabolic Explorer Procede de preparation de microorganismes evolues permettant la creation ou la modification de voies metaboliques
US7745195B2 (en) 2003-02-18 2010-06-29 Metabolic Explorer Method for the preparation of an evolved microorganism for the creation or the modification of metabolic pathways
EP1496111A2 (de) 2003-07-10 2005-01-12 Consortium für elektrochemische Industrie GmbH Varianten der 3-Phosphoglyceratdehydrogenase mit reduzierter Hemmung durch L-Serin und dafür codierende Gene
US7582460B2 (en) 2003-07-10 2009-09-01 Wacker Chemie Ag 3-phosphoglycerate dehydrogenase variants whose inhibition by L-serine is reduced, and genes encoding them
US20070087403A1 (en) 2003-11-06 2007-04-19 Bestel-Corre Gwenaelle Optimised micro-organism strains for nadph-consuming biosynthetic pathways
WO2005047498A1 (fr) 2003-11-06 2005-05-26 Metabolic Explorer Souches de microorganismes optimisees pour des voies de biosynthese consommatrices de nadph
WO2005073364A2 (fr) 2004-01-12 2005-08-11 Metabolic Explorer Microorganisme evolue pour la production de 1,2-propanediol
US20070072279A1 (en) 2004-01-12 2007-03-29 Isabelle Meynial-Salles Evolved micro-organisms for the production of 1,2-propanediol
WO2005111202A1 (en) 2004-05-12 2005-11-24 Metabolic Explorer Recombinant enzyme with altered feedback sensitivity
US20090029424A1 (en) 2004-05-12 2009-01-29 Metabolic Explorer Recombinant enzyme with altered feedback sensitivity
WO2006082252A2 (en) 2005-02-07 2006-08-10 Metabolic Explorer Method for the enzymatic production of alpha-ketobutyrate
WO2006082254A2 (en) 2005-02-07 2006-08-10 Metabolic Explorer Microorganisms comprising enzymes expressed with low gamma-elimination activity
US20080286840A1 (en) 2005-02-07 2008-11-20 Rainer Figge Microorganisms Comprising Enzymes Express with Low Gamma-Elimination Activity
US20080233617A1 (en) 2005-08-11 2008-09-25 Rainer Figge Process for the Preparation of a Aspartate and Derived Amino Acids Like Lysine, Threonine, Isoleucine, Methionine, or Homoserine Employing Microorganism with Enhanced Isocitrate Lyase and/or Malate Synthase Expression
WO2007017710A1 (en) 2005-08-11 2007-02-15 Metabolic Explorer Process for the preparation of aspartate and derived amino acids like lysine, threonine, isoleucine, methionine, homoserine, or valine employing a microorganism with enhanced isocitrate lyase and/or malate synthase expression
WO2007077041A1 (en) 2006-01-04 2007-07-12 Metabolic Explorer Process for the preparation of methionine and its precursors homoserine or succinylhomoserine employing a microorganism with enhanced sulfate permease expression
US20080311632A1 (en) 2006-01-04 2008-12-18 Rainer Figge Methods for Producing Methionine by Culturing a Microorganism Modified to Enhance Production of Cysteine
US20070259411A1 (en) * 2006-05-05 2007-11-08 Bramucci Michael G Solvent tolerant microorganisms and methods of isolation
WO2007141316A2 (en) 2006-06-09 2007-12-13 Metabolic Explorer Glycolic acid production by fermentation from renewable resources
US20090155867A1 (en) 2006-06-09 2009-06-18 Philippe Soucaille Glycolic Acid Production by Fermentation from Renewable Resources
US20090325245A1 (en) 2006-06-12 2009-12-31 Philippe Soucaille Ethanolamine Production by Fermentation
WO2007144346A1 (en) 2006-06-12 2007-12-21 Metabolic Explorer Ethanolamine production by fermentation
US20080085558A1 (en) 2006-10-03 2008-04-10 Philippe Soucaille Process for Chromosomal Integration and DNA Sequence Replacement in Clostridia
WO2008040387A1 (en) 2006-10-03 2008-04-10 Metabolic Explorer Process for chromosomal integration and dna sequence replacement in clostridia
WO2008052973A2 (en) 2006-10-31 2008-05-08 Metabolic Explorer Process for the biological production of n-butanol with high yield
WO2008052595A1 (en) 2006-10-31 2008-05-08 Metabolic Explorer Process for the biological production of 1,3-propanediol from glycerol with high yield
US20100086982A1 (en) 2006-10-31 2010-04-08 Metabolic Explorer PROCESS FOR THE BIOLOGICAL PRODUCTION OF n-BUTANOL WITH HIGH YIELD
US20100137655A1 (en) 2006-10-31 2010-06-03 Metabolic Explorer Process for the biological production of 1,3-propanediol from glycerol with high yield
WO2008115840A2 (en) 2007-03-16 2008-09-25 Genomatica, Inc. Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
Anderson; "Growth Requirements of Virus-Resistant Mutants of Escherichia coli Strain "B""; Department of Biology; 1946; Proc. Natl. Acad Sci; USA; pp. 120-128.
Atsumi et al. Engineering the isobutanol biosynthetic pathway in Escherichia coli by comparison of three aldehyde reductase/alcohol dehydrogenase genes. Appl Microbiol Biotechnol. Jan. 2010;85(3):651-7. doi: 10.1007/s00253-009-2085-6. Epub Jul. 16, 2009. *
Atsumi et al. Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels. Nature. Jan. 3, 2008;451(7174):86-9. doi: 10.1038/nature06450. *
Ballou et al; "The Synthesis and Properties of Hydroxypyruvic Acid Phosphate" 1956; J. Am Chem Soc; vol. 78; pp. 3718-3720.
Branden et al. Introduction to Protein Structure, Garland Publishing Inc., New York, p. 247, 1991. *
Datsenko et al.; "One-Step Inactivation of Chromosomal Genes in Escherichia coli K-12 Using PCR Products"; PNAS; 2000; vol. 97; No. 12; pp. 6640-6645.
Harrington et al.; "Balanced Branching in Transcription Termination"; PNAS; 2001; vol. 98; No. 9; pp. 5019-5024.
International Search Report of PCT/EP2009/067994, dated Apr. 6, 2010.
Korte et al.; "Alpha-Hydroxyalkyliden-Lacton-Umlagerung in Waessriger Salzsaeure"; 1959; Chem Ber; pp. 877-883.
Lane et al.; "2-Keto-4-Hydroxybutyrate. Synthesis, Chemical Properties, and as a Substrate for Lactate Dehydrogenase of Rabbit Muscle"; 1969; Biochemistry; pp. 2958-2966.
Lee et al.; "Global Analyses of Transcriptomes and Proteomes of a Parent Strain and an L-Threonine-Overproducing Mutant Strain"; Journal of Bacteriology; 2003; vol. 185; No. 18; pp. 5442-5451.
Lerner et al.; "Low Number Plasmids for Regulated Low-Level Expression of Cloned Genes in Escherichia coli With Blue/White Insert Screening Capability"; Nucleic Acids Research; vol. 18; No. 15; 1990; p. 4631.
Li et al.; "Enhanced Activity of yqhD Oxidoreductase in Synthesis of 1,3-Propanediol by Error-Prone PCR"; Progress in Natural Science 18; 2008; pp. 1519-1524.
Liebl et al.; "Requirement of Chelating Compounds for the Growth of Corynebacterium Glutamicum in Synthetic Media"; Appl Microbiol Biotechnol; 1989; 32:205-210.
Miller; "A Short Course in Bacterial Genetics: A Laboratory Manual and Handbook for Escherichia coli and Related Bacteria"; Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; 1992 (Book).
Norrander et al.; "Construction of Improved M13 Vectors Using Oligodeoxynucleotide-Directed Mutagenesis"; Gene; 1983; pp. 101-106.
Paul et al.; "Transposition Des Dihydro-2.5 Furannes En Dihydro-2.3 Furannes.-Application a La Preparation De L'Hydroxy-4 Butanal"; Bulletin De La Societe Chimique De France' 1950; pp. 668-671.
Riedel et al.; "Characterization of the Phosphoenolpyruvate Carboxykinase Gene From Corynebacterium Glutamicum and Significance of the Enzyme for Growth and Amino Acid Production"; J. Mol. Microbiol. Biotechnol.; 2001; 3(4): 573-583.
Schaefer et al.; "Automated Sampling Device for Monitoring Intracellular Metabolite Dynamics"; Analytical Biochemistry; 270; 1999; pp. 88-96.

Also Published As

Publication number Publication date
EP2379730B1 (de) 2015-07-22
JP2012513760A (ja) 2012-06-21
JP5774493B2 (ja) 2015-09-09
KR20170049612A (ko) 2017-05-10
ES2549003T3 (es) 2015-10-22
CN102341502A (zh) 2012-02-01
KR101827230B1 (ko) 2018-02-07
WO2010076324A1 (en) 2010-07-08
US20110294178A1 (en) 2011-12-01
KR20110117131A (ko) 2011-10-26
CN102341502B (zh) 2015-07-01
BRPI0923748B1 (pt) 2019-04-09
BRPI0923748A2 (pt) 2015-08-18
PT2379730E (pt) 2015-10-16
MX2011007039A (es) 2011-07-20
EP2379730A1 (de) 2011-10-26

Similar Documents

Publication Publication Date Title
US9121041B2 (en) Method for the preparation of diols
US8911978B2 (en) Method for the preparation of hydroxy acids
US8900838B2 (en) Method for the preparation of 1,3-propanediol from sucrose
US20110151530A1 (en) Enzymatic production of 2-hydroxy-isobutyrate (2-hiba)
US10385322B2 (en) Mutant glutamate dehydrogenase for the conversion of homoserine into 4-hydroxy-2-ketobutyrate
JP2007517517A (ja) １，２−プロパンジオールの産生のための発展型微生物
KR102149044B1 (ko) 2-히드록시 감마 부티로락톤 또는 2,4-디히드록시-부티레이트 의 제조 방법
EP2872639B1 (de) Modifizierter mikroorganismus zur herstellung von 1,3-propandiol
US11162082B2 (en) Mutant phosphoserine aminotransferase for the conversion of homoserine into 4-hydroxy-2-ketobutyrate
EP2540834A1 (de) Verfahren zur Herstellung von 1,3-Propandiol

Legal Events

Date Code Title Description
AS Assignment

Owner name: METABOLIC EXPLORER, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SOUCAILLE, PHILIPPE;REEL/FRAME:026721/0653

Effective date: 20110712

STCF Information on status: patent grant

Free format text: PATENTED CASE

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4

FEPP Fee payment procedure

Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

LAPS Lapse for failure to pay maintenance fees

Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20230901